On October 19, 1987, I was a 24-year-old financial planner with about a year under my belt. By the closing bell, that day had the name it still carries: Black Monday. The market fell 20.5% in a single session — the largest one-day drop in history to that point. My clients were scared and angry. So was I. I didn’t have the perspective yet to steady anyone, and the truth is it scared me out of the business entirely.
That could have been the end of the story. It wasn’t.
I returned to financial services in 2003 as a life insurance agent, and later built a career as an Enrolled Agent — a tax accountant. From the outside, things looked settled.
Then came July 11, 2018. I went to work like any other morning. By that evening I was in the emergency room with the worst pain of my life. Two weeks later, I nearly died. What followed was 100 days of surgery and recovery. I was 55, and for the first time I had to sit still long enough to ask what I wanted the rest of my life to look like.
My wife and I asked that question together. It changed how we saw our future, our work, and what we wanted from the years ahead. And as much as I respected what I’d built, one thing was clear: it didn’t include doing tax returns.
What I realized surprised me. I love financial services — not the filings, the people. So I stopped preparing returns but carried the tax knowledge with me. It now informs nearly every plan I build, because how money is taxed shapes how much you actually keep. Most of all, I love helping people see that much of what they believe about money simply isn’t true.
Why do we hold beliefs about money that don’t serve us? The biggest reason, I think, is that we operate by rules taught to us by the institutions we depend on — banks, lenders, credit card companies, insurers, investment firms. They run for their own best interest, as they should. But that raises a more important question: is the way they’ve taught you to handle your money actually in your best interest?
That question is the heart of everything I do now.
Today, my life is aligned with who I really am. I’m building sustainable wealth for my family and the generations after us — and I coach families who want the same: people tired of guessing, tired of conflicting advice, and ready to feel in control of their financial future.
The Black Monday version of me couldn’t have done this work; he didn’t have the scars yet. Surviving a crash that shook my confidence, then something far more serious that nearly ended my life, taught me what most financial advice skips over: money decisions are never just math. They’re about fear, family, legacy, and the freedom to live the life you actually want.
So when I sit down with a family, I’m not there to sell a product or push a transaction. I’m there as a guide — someone who has been frightened by the markets, humbled by his own mortality, and come out the other side with conviction about what matters. My job is to help you ask better questions, challenge the assumptions you didn’t know you were carrying, and build a plan that serves you and the people you love.
I took a long time finding my way to this work, and I’m not going anywhere now. My career, it turns out, is my calling — and I’d be honored to help you think differently about yours.
Chris Pruitt helps families take a fresh look at the money rules they’ve been handed — and decide which ones actually serve them. He offers a complimentary strategy session for readers who’d like a second opinion on their own plan.
